(Z)-3-iodo-3-(quinolin-3-yl)prop-2-en-1-ol | 948997-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (Z)-3-iodo-3-(quinolin-3-yl)prop-2-en-1-ol
• 英文别名: (Z)-3-iodo-3-quinolin-3-ylprop-2-en-1-ol
• CAS: 948997-58-8
• 化学式: C₁₂H₁₀INO
• 分子量: 311.122
• InChiKey: ZHDZMILKJWWVBS-WZUFQYTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-iodo-3-(quinolin-3-yl)prop-2-en-1-ol 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四溴化碳 、 三叔丁基膦 、 caesium carbonate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  E/Z Isomerization of 3,3-disubstituted allylic thioethers

  摘要：

  Allylic thioethers of the general structure 1 underwent E/Z isomerization during both basic and acidic hydrolysis of the ester moiety at the remote end of the molecule. The isomerization was dependent on the substitution of the allylic moiety. The presence of a 5-membered heterocycle on the double bond supported the isomerization. However, analogous oxy-ethers were stable. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.164
• 作为产物：
  描述：

  3-(3-quinolinyl)-2-propyn-1-ol 在 lithium aluminium tetrahydride 、 乙酸乙酯 、 碘 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-3-iodo-3-(quinolin-3-yl)prop-2-en-1-ol
  参考文献：
  名称：

  E/Z Isomerization of 3,3-disubstituted allylic thioethers

  摘要：

  Allylic thioethers of the general structure 1 underwent E/Z isomerization during both basic and acidic hydrolysis of the ester moiety at the remote end of the molecule. The isomerization was dependent on the substitution of the allylic moiety. The presence of a 5-membered heterocycle on the double bond supported the isomerization. However, analogous oxy-ethers were stable. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.164

文献信息

• Novel selective PPARδ agonists: Optimization of activity by modification of alkynylallylic moiety
  作者：Miroslav Havranek、Per Sauerberg、John P. Mogensen、Pavel Kratina、Claus B. Jeppesen、Ingrid Pettersson、Pavel Pihera

  DOI：10.1016/j.bmcl.2007.05.051

  日期：2007.8

  Y-shaped molecules bearing alkynylallylic moieties were found to be potent and selective PPAR delta activators. The alkynylallylic moiety was synthesized from alkyn-l-ols by hydroalumination followed by a cross-coupling reaction. Series of active compounds 6 were obtained by stepwise changing the structure of the known PPARpan agonist 5 into Y-shaped compounds. The most active and selective compound, 6f, had a PPAR delta potency of 0.13 mu M, which is 50-fold more potent than compound 5. (c) 2007 Elsevier Ltd. All rights reserved.